Cinnamon lollipop

when your licking a booty hole and you get poop on your tongue.

I tossed John's salad but it turned out to be a cinnamon lollipop!

by The dirrty crew April 29, 2020

chocolate lollipop

when you insert a lollipop into a womans asshole and then eat the lollipop

we did the chocolate lollipop last night. tasted awful tho.

by lincummaster October 14, 2021

lollipoping

when a girl is giving a guy head and she inserts a stick into his urethra and continues to suck his tip from the side.

She scared the shit outta me when she went down and started lollipoping me!

by Doikster October 02, 2021

Columbian Lollipop

A condom filled with cocaine that is inserted into ones anus.

He was busted at the airport for having 5 Columbian lollipops.

by Sparky Nelson April 30, 2019

Midwest Lollipop

An alternative to I-70 or I-80 road head. The name for the act of getting suddenly blindfolded and tied up by your girlfriend in a two-star midwestern hotel off the highway; so she can whack you with a potholder, then fellate and ride your lollipop, while you lie there unable to thwart her fast food and White Claw-fueled demands.

“It was a long drive back to Colorado, but I gave him the Midwest Lollipop to break up the monotony.”

“Driving through the Midwest is tediously boring, but the GF gave me the Midwest Lollipop when we overnighted in Omaha.”

“Welcome to Iowa. Home of the Midwest Lollipop.”

by MammaCitaMeowMeow March 18, 2022

lollipop lick

When a guy cums all over his own dick and the partner licks it off.

Dude my girl loves to Lollipop lick me.

by Snix363 November 28, 2015

Lollipop Sisters

Two women that have have sex with the same guy.

We are lollipop Sisters.

by July 10, 2023